25 Male Actors Playing Female Characters (Before Adam Sandler)

25 Male Actors Playing Female Characters (Before Adam Sandler)

Remember when Adam Sandler did Shakespeare? In “Billy Madison” the title character does a bit of “Hamlet.” Now Sandler is channeling the Bard again by portraying a female character in the new comedy “Jack and Jill.” He actually performs two roles, identical twin siblings, which was also not uncommon in Shakespeare’s time, I think. Though certainly not at the same time. But he’s getting more attention for taking on the sister part, Jill, because he makes a rather unattractive woman, and not just physically.

Back in the Elizabethan era only men could act and so they had to take on both male and female parts. Since the dawn of cinema, this hasn’t been the case, and therefore not a whole lot of cross-gender performances have made it to the big screen, relatively speaking anyway. Some people would say there are still too many.

I’m not talking about actors playing men who end up in drag, a la “Mrs. Doubtfire” or “Tootsie.” I’m talking actual opposite-gender roles, the kind that won Linda Hunt an Oscar and earned John Travolta his sixth Golden Globe nomination. Because this list is tied to Sandler’s new film, though, let’s just concentrate on the man-as-woman gigs, which really seem to have increased substantially since the mid ’80s. Is it John Waters’ influence or are all these mostly comic actors trying to copy Hunt’s success?

Or are they all paying tribute to one of the first great film comedians? It all begins with…

Charlie Chaplin

In one of Chaplin’s earliest short films, 1914’s “A Busy Day” (also known as “Militant Suffragete“), he played the jealous ‘Wife’ to Mack Swain’s ‘Husband.’ Back then you could really hide your masculinity inside of all those clothes. Basically there’s a lot of kicking and slapping as she interferes with a film set, and then she falls into the harbor. Watch the whole film below:

Wallace Beery

Beery portrayed the female character Sweedie the Maid in more than 25 films for Essanay between 1914 and 1916, long before his more well-known works like The Champ and Viva Villa!The quite masculine actor had regularly played old ladies in vaudeville, and this cross-gender performance specialty simply continued into his early film career. The “Sweedie” films were also where he met his first wife, then-teenage Gloria Swanson, who he was allegedly terrible to. Check out a few images from “Topsy-Turvy Sweedie”found at NitrateVille.com. And here is a tiny bit of “Sweedie Learns to Swim” with Ben Turpin:

Fatty Arbuckle

The original obese comedy star played the daughter of a mothball magnate in “Miss Fatty’s Seaside Lovers” (1915). In the one-reel film, which Arbuckle also directed, the clashingly clothed young woman tags along with her family to a sea resort, where like Chaplin’s ‘Wife’ she ends up in the water. Among her suitors who attempt to rescue her is a pre-star Harold Lloyd. Lloyd would of course do his own drag stunts over the years, but I don’t think he ever played an actual female character.

Arthur Lucan

Basically the Tyler Perry of his time, and also a follow-up to Beery, Lucan developed his own elderly woman character, Old Mother Riley, in Irish music halls during the 20s and 30s. Like most stage acts of the time, the actor made his way to the screen once sound pictures came about. He was joined by his partner and wife, Kitty McShane, who always played Mother Riley’s daughter (I wonder if this ever led to kinky bedroom play…). The film series ran from 1937’s “Old Mother Riley” to 1952’s “Mother Riley Meets the Vampire,” after which he continued a couple more years portraying the character on stage. He was set to bring Mother Riley into outer space for another film, but he died before it could become a reality. Hopefully Madea will go to Mars in her place one day. Watch the 1943 sequel “Old Mother Riley Detective” in full below:

Alec Guinness

In one of the classic comedies of all time, “Kind Hearts and Coronets” (1949), the future Obi-Wan Kenobi plays eight separate roles among the D’Ascoyne family, including Lady Agatha D’Ascoyne, the suffragette whose feminist agenda is thwarted by a revenge plot to rid the whole clan. Of course, her feminity was already thwarted by Guinness’s interest in playing numerous parts, an idea that would come back decades later (keep reading).

Alastair Sim

Another multi-role performance comes from Sim in the first “St. Trinian’s” comedy, “The Belles of St. Trinian’s” (1954), though he’s mostly remembered for the female part of the school’s permissive headmistress, Milicent Fritton. He reprised the character in a cameo in the second installment, “Blue Murder at St. Trinian’s” (1957). This would be paid homage fifty years later in a reboot of the franchise (keep reading).

Jerry Lewis

Of course Jerry Lewis did a cross-gender role. In fact, he did six (remember this doesn’t count all his drag bits). In “Three on a Couch” (1966), his much-despised first film for Columbia Pictures, he takes on four extra parts besides his starring role, one of which is the redheaded bug lover, Heather. You can see the bit in motion in the trailer below. Earlier, Lewis played his own character’s mother in “The Ladies Man” (1960) and three horrible female backup singers in “The Patsy” (1964). Later, he played a middle-aged woman character in the 1981 film “Hardly Working.” See him as Heather in the clip below, beginning at about 5:00.

Akihiro Miwa (aka Akihiro Maruyama)

Japan’s most famous female impersonator, Miwa can nowadays be heard here in the non-dubbed versions of Hiyao Miyazaki films. Decades earlier he convincingly starred as a femme fatale in “Black Rose Mansion” (1969) and an elusive female criminal in “Black Lizard” (1968), both directed by Kinji Fukasaku. A successful songwriter and cabaret singer, he also composed the theme song for the latter and can be seen crooning in the former (in an unembeddable YouTube clip). Here’s a section of his performance as the title character in “Black Lizard”:

Barry Humphries

If you don’t know the name Barry Humphries, you might at least know his alter ego, Dame Edna Everage. The character debuted as a club act before hitting the big screen with 1972’s “The Adventures of Barry McKenzie” followed by a 1974 sequel, “Barry McKenzie Holds His Own,” in which he went from being just Aunt Edna to Dame Edna. Now the character is so well known that he’s often credited as her instead of himself, and it merely seems like Humphries’ drag personality rather than a qualifiable female film role. Well, he also portrayed an old lady in the 2002 adaptation of “Nicholas Nickleby.” A trailer for “Holds His Own” starring ‘Edna’:

Terry Jones

Most, if not all, of the Monty Python players regularly portrayed female characters, but Jones is typically the one I most associate as the woman of the group. I guess because he’s best at doing a really high alto voice, and the most prominate image I have of him is as Brian’s mother in “Life of Brian” (1979). He’s just an old mother. He plays one in “Monty Python and the Holy Grail” (1974), and in “The Meaning of Life” (1983) and even voices one in “L.A. Story” (1991). Let him stand in for all comedy troupes in which men play female roles, whether it be “The State,” “The Kids in the Hall” or any other. A great bit from “Life of Brian”:

Tamasaburo Bando

Can I slip in a little obscure foreign fantasy film before continuing with the comedies? In “Yasha-ga-ike” (“Demon Pond,” 1979), kabuki actor Bando plays two female characters, a villager and a demonic princess. The film’s performances overall are done in the kabuki style, which interestingly enough began as an all-female artform that later led to an all-male version. This film, however, does feature actors of both sexes. You can get a tiny idea of his performance in this bad-quality clip.

Pîtâ (aka Peter)

Another Japanese film (co-produced by the French), “Fruits of Passion” (1981) has the honor of starring Klaus Kinski (who does a bit of drag in “Crawlspace”). But let’s focus. Co-starring is Shinnosuke Ikehata, credited as Peter but now better known as Pîtâ, who is best known here for playing the fool, Kyoami, in Kurosawa’s “Ran.” I think ‘he’ may be technically considered a transvestite, so perhaps ‘she’ is the correct term. But does that make her an actress not an actor? Either way, in “Fruits” she is well regarded in the role of a brothel Madame.

Divine

One of the most famous drag queens in history, Divine (aka Harris Milstead) portrayed a number of women throughout his career, including and most notably in the cult films of John Waters. From the smoking nun in Waters’ early work “Roman Candles” to the more mainstream “Hairspray” (1988), released just weeks after her death, she also can’t be forgotten in roles as Babs Johnson (“Pink Flamingos”), Dawn Davenport (“Female Trouble”) and Francine Fishpaw (“Polyester”). Of course, “Hairspray”‘s Edna Turnblad would become the most iconic thanks to later portrayals of the character (keep reading). Edna, trying to iron in here:

Arsenio Hall

Strangely, given some of his later films, Eddie Murphy did not portray any female roles in “Coming to America” (1988). He and Arsenio Hall took on four parts apiece making them each only half the man Guinness was forty years earlier. Is the joke in the scene featuring his character ‘Extremely Ugly Girl’ that she’s supposed to be assumed to be a man in drag? If so, she might not fit this list after all.

Michael J. Fox

Another question: why is it that in “Back to the Future Part II” (1989) the offspring of Marty McFly and Jennifer only look like clones of Marty? Obviousy so that Michael J. Fox could hilariously play multiple characters, including his daughter Marlene. Speaking of which, what kind of butthead names his daughter Marlene if his name is Marty and his son’s name is Marty Jr.? I guess it’s assumed that the kids are twins and so have similar names. Okay, here’s another question: why is the wife of Marty’s ancestor, Seamus McFly, a spot-on likeness of his mother? Is she a Baines? Was there incest going on around Hill Valley?

Mostly famous for Tilda Swinton’s androgenous and gender-swapping performance as the title characer, “Orlando” (1992) also fittingly had the opposite sort of stunt in Crisp’s early-on portrayal of the Elizabeth I just before her death. Many actresses have been amazing as the Virgin Queen, but this might be the most perfect, just like how Cate Blanchett was the best impersonator of Bob Dylan.

RuPaul

Probably the most famous drag queen of today, RuPaul has portrayed women in a few films, including “Crooklyn,” but his teacher character in the two “Brady Bunch” movies, 1995’s “The Brady Bunch Movie” and 1996’s “A Very Brady Sequel,” is the one most certainly known to definitely be female, not a man in drag. Unless the daughters seen with Mrs. Cummings in the sequel are adopted.

Eddie Murphy

At last Murphy made up for his lack of female portrayal in “Coming to America” by playing two women, Mama and Granny, among the many in the Klump clan in both “The Nutty Professor” (1996) and “The Nutty Professor II: The Klumps” (2000). Actually, it was better before he went there. The fat suit thing was enough without the added on multi-role gimmick, which mostly consisted of the tired simplicity of men dressing up as old, overweight ladies. I’d like to go back to “BTTF2” and congratulate Michael J. Fox for one of the few young — and I’ll say it, attractive — female portrayals. Okay, that’s not right to say. I’m sure someone out there thinks Rasputia from “Norbit” (2007) is hot. And better in Spanish:

Charles Busch

Like Divine, Busch is a product of the campy cult drag scene and while he does do some roles as men who dress as women, he’s best known for “Die Mommie Die” (2003), in which he reprises his stage role (which he also wrote) as lounge singer Angela Arden. Earlier he appeared in the 2000 adaptation of his play “Psycho Beach Party,” though his original part was given to an actress (Lauren Ambrose) and he took on the role of a female police detective.This time it’s for her:

Jack Plotnick, Clinton Leupp and Jeffery Roberson

It’s unfortuante that while some other more famous actors are getting their own entry in this list, these three are lumped together. But their portrayals, respectively, as Evie, Coco and Varla in “Girls Will Be Girls” (2003) go hand in hand in hand. So much that they’ve shared both Best Actor and Best Actress honors at different film fests. A five-episode web series followed the film and there’s finally a Kickstarter-funded sequel on the way soon. Even though this video, of the episode “Girl Stalk, Part 1,” isn’t from the movie, it’s the best quality look at the trio:

Tyler Perry

Doubtfully conscious, Perry’s own evolution from playing women on the stage and then film (starting with 2005’s “Diary of a Mad Black Woman”) recalls the career of Beery. Eventually there will probably be as many feature films involving Mabel ‘Madea’ Simmons as there were shorts about Sweedie. But will Perry ever get an Oscar for a boxing movie? Oh darn, I’ve now given him an idea for “Madea’s Knock Out.” I’m not sure what this clip is from, but it’s the only good clip I could find without an ad before it:

John Travolta

Following Divine there have been many men, and I believe only men, who’ve portrayed Edna Turnblad. On stage for the musical versionthere was George Wendt, Michael McKean, Harvey Fierstein, Michael Ball, Bruce Vilanch and others. Then came the film adaptation of the show adaptation of the movie, in which Travolta took to the wig, dress and fat suit. I never saw it, mainly because of him. I don’t care that he earned awards for it, his whole look is just too distracting in my opinion. And the singing voice here is atrocious:

Rupert Everett

Paying proper tribute to the original “St. Trinian’s” films, Everett does as Sim did and portrays the school’s current headmistress, Camilla Dagey Fritton, as a butch old lady who continues to run things rather loosely. In “St. Trinian’s” (2007), he also, like Sim, plays her brother. But in the sequel, “St. Trinian’s 2: The Legend of Fritton’s Gold” (2009), the actor is given even more to do, rather than just a cameo, including playing a pirate ancestor and an old Reverend relative. A third movie is in the works, but it’s unknown how many and what gender roles Everett will have in that one. See him as Camilla at the start of this section from the first film: